Acetic Acid → N-Ethylcarbamate 5-cyclopropylmethoxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 508527Notes

Reaction equation

HRID 508527 reaction equation
C1C(=O)N([Cl:8])C(=O)C1.C(O)(=O)C.[CH2:13]([NH:15][C:16](=[O:18])[O-:17])[CH3:14].[CH:19]1([CH2:22][O:23][C:24]2[CH:25]=[CH:26][C:27]3[CH:28]([CH3:36])[CH:29]4[CH2:33][NH:32][CH2:31][CH:30]4[C:34]=3[CH:35]=2)[CH2:21][CH2:20]1>ClCCCl>[CH2:13]([NH:15][C:16](=[O:17])[O-:18])[CH3:14].[CH:19]1([CH2:22][O:23][C:24]2[C:25]([Cl:8])=[CH:26][C:27]3[CH:28]([CH3:36])[CH:29]4[CH2:33][NH:32][CH2:31][CH:30]4[C:34]=3[CH:35]=2)[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 31398ChlorosuccinimideHCID 86602865N-Ethylcarbamate 5-cyclopropylmethoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Product 1

HCID 86602866N-Ethylcarbamate 5-cyclopropylmethoxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

NCS (38 mg, 0.28 mmol) and acetic acid (1 mL) were added to a solution of N-ethylcarbamate-5-cyclopropylmethoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (89 mg, 0.28 mmol) in DCE (2 mL), and the reaction solution was stirred for 3 hours at 70° C. The reaction was quenched with H2O and the solution filtered through an Extrelut column. The column was washed with CH2Cl2, and the filtrate was concentrated. The subtitle compound was obtained without further purification. MS calculated for C19H24ClNO3+H: 350, observed: 350.

Workup

  1. customThe reaction was quenched with H2O
  2. filtrationthe solution filtered through an Extrelut column
  3. washThe column was washed with CH2Cl2
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f0c17f462d30403ca539377f70bed2b1
Source dataset
uspto-grants-2015_08
Patent number
US09096520B2

Reaction notes

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